5-fluoro-2-oxopyrimidine-1(2H)-carboxylate derivatives

ABSTRACT

This present disclosure is related to the field of 5-fluoro-2-oxopyrimidine-1-(2H)-carboxylates and their derivatives and to the use of these compounds as fungicides.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional PatentApplication Ser. No. 61/232,232 filed Aug. 7, 2009.

BACKGROUND AND SUMMARY OF THE INVENTION

Fungicides are compounds, of natural or synthetic origin, which act toprotect and/or cure plants against damage caused by agriculturallyrelevant fungi. Generally, no single fungicide is useful in allsituations. Consequently, research is ongoing to produce fungicides thatmay have better performance, are easier to use, and cost less.

The present disclosure relates to5-fluoro-2-oxopyrimidine-1(2H)-carboxylate compounds and their use asfungicides. The compounds of the present disclosure may offer protectionagainst ascomycetes, basidiomycetes, deuteromycetes and oomycetes.

One embodiment of the present disclosure may include compounds ofFormula I:

wherein R¹ is:

-   -   H;    -   C₁-C₆ alkyl optionally substituted with 1-3 R⁴;    -   C₁-C₆ alkenyl optionally substituted with 1-3 R⁴;    -   C₃-C₆ alkynyl optionally substituted with 1-3 R⁴;    -   phenyl or benzyl wherein each of the phenyl or the benzyl may be        optionally substituted with 1-3 R⁵; or with a 5- or 6-membered        saturated or unsaturated ring system, or with a 5-6 fused ring        system, or with a 6-6 fused ring system each containing 1-3        heteroatoms wherein each ring may be optionally substituted with        1-3 R⁵, biphenyl or naphthyl optionally substituted with 1-3 R⁵;    -   —(CHR⁶)_(m)OR⁷;    -   —C(═O)R⁸;    -   —C(═S)R⁸;    -   —S(O)₂R⁸;    -   —C(═O)OR⁸;    -   —C(═S)OR⁸;    -   —(CHR⁶)_(m)N(R⁹)R¹⁰;    -   —C(═O)N(R⁹)R¹⁰; or    -   —C(═S)N(R⁹)R¹⁰;        wherein m is an integer 1-3;        R² is H or C₁-C₆ alkyl optionally substituted with R⁴;        alternatively R¹ and R² may be taken together to form        ═CR¹¹N(R¹²)R¹³;        R³ is —C(═O)OR⁸ or —C(═S)OR⁸;        R⁴ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₄ haloalkylthio,        amino, halothio, C₁-C₃ alkylamino, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylcarbonyl, C₂-C₆ alkylaminocarbonyl, hydroxyl, or C₃-C₆        trialkylsilyl,        R⁵ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio,        amino, C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₆        alkoxycarbonyl, or C₂-C₆ alkylcarbonyl, nitro, hydroxyl, or        cyano, halothio;        R⁶ is H, C₁-C₆ alkyl, C₁-C₆ alkoxy, phenyl or benzyl wherein        each of the phenyl wherein each of the phenyl or the benzyl may        be optionally substituted with 1-3 R⁵;        R⁷ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxyalkyl, C₂-C₆ alkylcarbonyl, phenyl or        benzyl wherein each of the phenyl or the benzyl may be        optionally substituted with 1-3 R⁵, or with a 5- or 6-membered        saturated or unsaturated ring system, or with a 5-6 fused ring        system, or with a 6-6 fused ring system each containing 1-3        heteroatoms        wherein each ring may be optionally substituted with 1-3 R⁵,        biphenyl or naphthyl optionally substituted with 1-3 R⁵;        R⁸ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxyalkyl, —(CH₂)₂OCH₂(C₆H₅), phenyl or        benzyl wherein each of the phenyl or the benzyl may be        optionally substituted with 1-3 R⁵; or with a 5- or 6-membered        saturated or unsaturated ring system, or with a 5-6 fused ring        system, or with a 6-6 fused ring system each containing 1-3        heteroatoms wherein each ring may be optionally substituted with        1-3 R⁵, biphenyl or naphthyl optionally substituted with 1-3 R⁵;        R⁹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxyalkyl, C₂-C₆        alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or        the benzyl may be optionally substituted with 1-3 R⁵; or with a        5- or 6-membered saturated or unsaturated ring system, or with a        5-6 fused ring system, or with a 6-6 fused ring system each        containing 1-3 heteroatoms wherein each ring may be optionally        substituted with 1-3 R⁵, biphenyl or naphthyl optionally        substituted with 1-3 R⁵;        R¹⁰ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxyalkyl, C₂-C₆        alkylcarbonyl, benzyl, wherein the benzyl may be optionally        substituted with 1-3 R⁵;        alternatively R⁹ and R¹⁰ may be taken together to form a 5- or        6-membered saturated ring containing 1-3 heteroatoms wherein        each ring may be optionally substituted with 1-3 R⁵;        R¹¹ is H or C₁-C₄ alkyl;        R¹² is H cyano, hydroxyl, C₁-C₄ alkyl, C₁-C₆ alkoxy, C₂-C₆,        alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or        the benzyl may be optionally substituted with 1-3 R⁵; or with a        5- or 6-membered saturated or unsaturated ring system, or with a        5-6 fused ring system, or with a 6-6 fused ring system each        containing 1-3 heteroatoms wherein each ring may be optionally        substituted with 1-3 R⁵, biphenyl or naphthyl optionally        substituted with 1-3 R⁵;        alternatively R¹¹ and R¹² may be taken together to form a 5- or        6-membered saturated ring containing 1-3 heteroatoms wherein        each ring may be optionally substituted with 1-3 R⁵; R¹³ is H,        C₁-C₄ alkyl, C₁-C₆ alkoxy, C₂-C₆, alkylcarbonyl, phenyl or        benzyl wherein each of the phenyl or the benzyl may be        optionally substituted with 1-3 R⁵, or with a 5- or 6-membered        saturated or unsaturated ring system, or with a 5-6 fused ring        system, or with a 6-6 fused ring system each containing 1-3        heteroatoms wherein each ring may be optionally substituted with        1-3 R⁵, biphenyl or naphthyl optionally substituted with 1-3 R⁵;        and        alternatively R¹² and R¹³ may be taken together to form a 5- or        6-membered saturated ring containing 1-3 heteroatoms wherein        each ring may be optionally substituted with 1-3 R⁵.

Another embodiment of the present disclosure may include a fungicidalcomposition for the control or prevention of fungal attack comprisingthe compounds described below and a phytologically acceptable carriermaterial.

Yet another embodiment of the present disclosure may include a methodfor the control or prevention of fungal attack on a plant, the methodincluding the steps of applying a fungicidally effective amount of oneor more of the compounds described below to at least one of the fungus,the plant, an area adjacent to the plant, and the seed adapted toproduce the plant.

The term “alkyl” refers to a branched, unbranched, or cyclic carbonchain, including methyl, ethyl, propyl, butyl, isopropyl, isobutyl,tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl and the like.

The term “alkenyl” refers to a branched, unbranched or cyclic carbonchain containing one or more double bonds including ethenyl, propenyl,butenyl, isopropenyl, isobutenyl, cyclohexenyl, and the like.

The term “alkynyl” refers to a branched or unbranched carbon chaincontaining one or more triple bonds including propynyl, butynyl and thelike.

As used throughout this specification, the term ‘R’ refers to the groupconsisting of C₂₋₈ alkyl, C₃₋₈ alkenyl, or C₃₋₈ alkynyl, unless statedotherwise.

The term “alkoxy” refers to an —OR substituent.

The term “alkoxycarbonyl” refers to a —C(O)—OR substituent.

The term “alkylcarbonyl” refers to a —C(O)—R substituent.

The term “alkylsulfonyl” refers to an —SO₂—R substituent.

The term “haloalkylsulfonyl” refers to an —SO₂—R substituent where R isfully or partially substituted with Cl, F, I, or Br or any combinationthereof.

The term “alkylthio” refers to an —S—R substituent.

The term “haloalkylthio” refers to an alkylthio, which is substitutedwith Cl, F, I, or Br or any combination thereof.

The term “halothio” refers to a sulfur substituted with three or five Fsubstituents.

The term “alkylaminocarbonyl” refers to a —C(O)—N(H)—R substituent.

The term “dialkylaminocarbonyl” refers to a —C(O)—NR₂ substituent.

The term “alkylcycloalkylamino” refers to a cycloalkylamino substituentthat is substituted with an alkyl group.

The term “trialkylsilyl” refers to —SiR₃.

The term “cyano” refers to a —C≡N substituent.

The term “hydroxyl” refers to an —OH substituent.

The term “amino” refers to a —NH₂ substituent.

The term “alkylamino” refers to a —N(H)—R substituent.

The term “dialkylamino” refers to a —NR₂ substituent.

The term “alkoxyalkyl” refers to an alkoxy substitution on an alkyl.

The term “haloalkoxyalkyl” refers to an alkoxy substitution on an alkylwhich is fully or partially substituted with Cl, F, Br, or I, or anycombination thereof.

The term “hydroxyalkyl” refers to an alkyl which is substituted with ahydroxyl group.

The term “haloalkoxy” refers to an —OR—X substituent, wherein X is Cl,F, Br, or I, or any combination thereof.

The term “haloalkyl” refers to an alkyl, which is substituted with Cl,F, I, or Br or any combination thereof.

The term “haloalkenyl” refers to an alkenyl, which is substituted withCl, F, I, or Br or any combination thereof.

The term “haloalkynyl” refers to an alkynyl which is substituted withCl, F, I, or Br or any combination thereof.

The term “halogen” or “halo” refers to one or more halogen atoms,defined as F, Cl, Br, and I.

The term “hydroxycarbonyl” refers to a —C(O)—OH substituent.

The term “nitro” refers to a —NO₂ substituent.

Throughout the disclosure, reference to the compounds of Formula I isread as also including optical isomers and salts of Formula I, andhydrates thereof. Specifically, when Formula I contains a branched chainalkyl group, it is understood that such compounds include opticalisomers and racemates thereof. Exemplary salts include: hydrochloride,hydrobromide, hydroiodide, and the like. Additionally, the compounds ofFormula I may include tautomeric forms.

Certain compounds disclosed in this document can exist as one or moreisomers. It will be appreciated by those skilled in the art that oneisomer may be more active than the others. The structures disclosed inthe present disclosure are drawn in only one geometric form for clarity,but are intended to represent all geometric and tautomeric forms of themolecule.

It is also understood by those skilled in the art that additionalsubstitution is allowable, unless otherwise noted, as long as the rulesof chemical bonding and strain energy are satisfied and the productstill exhibits fungicidal activity.

Another embodiment of the present disclosure is a use of a compound ofFormula I, for protection of a plant against attack by a phytopathogenicorganism or the treatment of a plant infested by a phytopathogenicorganism, comprising the application of a compound of Formula I, or acomposition comprising the compound to soil, a plant, a part of a plant,foliage, and/or seeds.

Additionally, another embodiment of the present disclosure is acomposition useful for protecting a plant against attack by aphytopathogenic organism and/or treatment of a plant infested by aphytopathogenic organism comprising a compound of Formula I and aphytologically acceptable carrier material.

Additional features and advantages of the present invention will becomeapparent to those skilled in the art upon consideration of the followingdetailed description of the illustrative embodiments exemplifying thebest mode of carrying out the invention as presently perceived.

DETAILED DESCRIPTION OF THE PRESENT DISCLOSURE

The compounds of the present disclosure may be applied by any of avariety of known techniques, either as the compounds or as formulationscomprising the compounds. For example, the compounds may be applied tothe roots, seeds or foliage of plants for the control of various fungi,without damaging the commercial value of the plants. The materials maybe applied in the form of any of the generally used formulation types,for example, as solutions, dusts, wettable powders, flowableconcentrates, or emulsifiable concentrates.

Preferably, the compounds of the present disclosure are applied in theform of a formulation, comprising one or more of the compounds ofFormula I with a phytologically acceptable carrier. Concentratedformulations may be dispersed in water, or other liquids, forapplication, or formulations may be dust-like or granular, which maythen be applied without further treatment. The formulations can beprepared according to procedures that are conventional in theagricultural chemical art.

The present disclosure contemplates all vehicles by which one or more ofthe compounds may be formulated for delivery and use as a fungicide.Typically, formulations are applied as aqueous suspensions or emulsions.Such suspensions or emulsions may be produced from water-soluble, watersuspendable, or emulsifiable formulations which are solids, usuallyknown as wettable powders; or liquids, usually known as emulsifiableconcentrates, aqueous suspensions, or suspension concentrates. As willbe readily appreciated, any material to which these compounds may beadded may be used, provided it yields the desired utility withoutsignificant interference with the activity of these compounds asantifungal agents.

Wettable powders, which may be compacted to form water dispersiblegranules, comprise an intimate mixture of one or more of the compoundsof Formula I, an inert carrier and surfactants. The concentration of thecompound in the wettable powder may be from about 10 percent to about 90percent by weight based on the total weight of the wettable powder, morepreferably about 25 weight percent to about 75 weight percent. In thepreparation of wettable powder formulations, the compounds may becompounded with any finely divided solid, such as prophyllite, talc,chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein,gluten, montmorillonite clays, diatomaceous earths, purified silicatesor the like. In such operations, the finely divided carrier andsurfactants are typically blended with the compound(s) and milled.

Emulsifiable concentrates of the compounds of Formula I may comprise aconvenient concentration, such as from about 10 weight percent to about50 weight percent of the compound, in a suitable liquid, based on thetotal weight of the concentrate. The compounds may be dissolved in aninert carrier, which is either a water-miscible solvent or a mixture ofwater-immiscible organic solvents, and emulsifiers. The concentrates maybe diluted with water and oil to form spray mixtures in the form ofoil-in-water emulsions. Useful organic solvents include aromatics,especially the high-boiling naphthalenic and olefinic portions ofpetroleum such as heavy aromatic naphtha. Other organic solvents mayalso be used, for example, terpenic solvents, including rosinderivatives, aliphatic ketones, such as cyclohexanone, and complexalcohols, such as 2-ethoxyethanol.

Emulsifiers which may be advantageously employed herein may be readilydetermined by those skilled in the art and include various nonionic,anionic, cationic and amphoteric emulsifiers, or a blend of two or moreemulsifiers. Examples of nonionic emulsifiers useful in preparing theemulsifiable concentrates include the polyalkylene glycol ethers andcondensation products of alkyl and aryl phenols, aliphatic alcohols,aliphatic amines or fatty acids with ethylene oxide, propylene oxidessuch as the ethoxylated alkyl phenols and carboxylic esters solubilizedwith the polyol or polyoxyalkylene. Cationic emulsifiers includequaternary ammonium compounds and fatty amine salts. Anionic emulsifiersinclude the oil-soluble salts (e.g., calcium) of alkylaryl sulfonicacids, oil-soluble salts or sulfated polyglycol ethers and appropriatesalts of phosphated polyglycol ether.

Representative organic liquids which may be employed in preparing theemulsifiable concentrates of the compounds of the present invention arethe aromatic liquids such as xylene, propyl benzene fractions; or mixednaphthalene fractions, mineral oils, substituted aromatic organicliquids such as dioctyl phthalate; kerosene; dialkyl amides of variousfatty acids, particularly the dimethyl amides of fatty glycols andglycol derivatives such as the n-butyl ether, ethyl ether or methylether of diethylene glycol, and the methyl ether of triethylene glycoland the like. Mixtures of two or more organic liquids may also beemployed in the preparation of the emulsifiable concentrate. Organicliquids include xylene, and propyl benzene fractions, with xylene beingmost preferred in some cases. Surface-active dispersing agents aretypically employed in liquid formulations and in an amount of from 0.1to 20 percent by weight based on the combined weight of the dispersingagent with one or more of the compounds. The formulations can alsocontain other compatible additives, for example, plant growth regulatorsand other biologically active compounds used in agriculture.

Aqueous suspensions comprise suspensions of one or more water-insolublecompounds of Formula I, dispersed in an aqueous vehicle at aconcentration in the range from about 5 to about 50 weight percent,based on the total weight of the aqueous suspension. Suspensions areprepared by finely grinding one or more of the compounds, and vigorouslymixing the ground material into a vehicle comprised of water andsurfactants chosen from the same types discussed above. Othercomponents, such as inorganic salts and synthetic or natural gums, mayalso be added to increase the density and viscosity of the aqueousvehicle. It is often most effective to grind and mix at the same time bypreparing the aqueous mixture and homogenizing it in an implement suchas a sand mill, ball mill, or piston-type homogenizer.

Aqueous emulsions comprise emulsions of one or more water-insolublepesticidally active ingredients emulsified in an aqueous vehicle at aconcentration typically in the range from about 5 to about 50 weightpercent, based on the total weight of the aqueous emulsion. If thepesticidally active ingredient is a solid it must be dissolved in asuitable water-immiscible solvent prior to the preparation of theaqueous emulsion. Emulsions are prepared by emulsifying the liquidpesticidally active ingredient or water-immiscible solution thereof intoan aqueous medium typically with inclusion of surfactants that aid inthe formation and stabilization of the emulsion as described above. Thisis often accomplished with the aid of vigorous mixing provided by highshear mixers or homogenizers.

The compounds of Formula I can also be applied as granular formulations,which are particularly useful for applications to the soil. Granularformulations generally contain from about 0.5 to about 10 weightpercent, based on the total weight of the granular formulation of thecompound(s), dispersed in an inert carrier which consists entirely or inlarge part of coarsely divided inert material such as attapulgite,bentonite, diatomite, clay or a similar inexpensive substance. Suchformulations are usually prepared by dissolving the compounds in asuitable solvent and applying it to a granular carrier which has beenpreformed to the appropriate particle size, in the range of from about0.5 to about 3 mm. A suitable solvent is a solvent in which the compoundis substantially or completely soluble. Such formulations may also beprepared by making a dough or paste of the carrier and the compound andsolvent, and crushing and drying to obtain the desired granularparticle.

Dusts containing the compounds of Formula I may be prepared byintimately mixing one or more of the compounds in powdered form with asuitable dusty agricultural carrier, such as, for example, kaolin clay,ground volcanic rock, and the like. Dusts can suitably contain fromabout 1 to about 10 weight percent of the compounds, based on the totalweight of the dust.

The formulations may additionally contain adjuvant surfactants toenhance deposition, wetting and penetration of the compounds onto thetarget crop and organism. These adjuvant surfactants may optionally beemployed as a component of the formulation or as a tank mix. The amountof adjuvant surfactant will typically vary from 0.01 to 1.0 percent byvolume, based on a spray-volume of water, preferably 0.05 to 0.5 volumepercent. Suitable adjuvant surfactants include, but are not limited toethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols,salts of the esters or sulfosuccinic acids, ethoxylated organosilicones,ethoxylated fatty amines and blends of surfactants with mineral orvegetable oils. The formulations may also include oil-in-water emulsionssuch as those disclosed in U.S. patent application Ser. No. 11/495,228,the disclosure of which is expressly incorporated by reference herein.

The formulations may optionally include combinations that contain otherpesticidal compounds. Such additional pesticidal compounds may befungicides, insecticides, herbicides, nematocides, miticides,arthropodicides, bactericides or combinations thereof that arecompatible with the compounds of the present invention in the mediumselected for application, and not antagonistic to the activity of thepresent compounds. Accordingly, in such embodiments, the otherpesticidal compound is employed as a supplemental toxicant for the sameor for a different pesticidal use. The compounds of Formula I and thepesticidal compound in the combination can generally be present in aweight ratio of from 1:100 to 100:1.

The compounds of the present disclosure may also be combined with otherfungicides to form fungicidal mixtures and synergistic mixtures thereof.The fungicidal compounds of the present disclosure are often applied inconjunction with one or more other fungicides to control a wider varietyof undesirable diseases. When used in conjunction with otherfungicide(s), the presently claimed compounds may be formulated with theother fungicide(s), tank mixed with the other fungicide(s) or appliedsequentially with the other fungicide(s). Such other fungicides mayinclude 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol,8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin,Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis,Bacillus subtilis strain QST713, benalaxyl, benomyl,benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) salt,bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen,blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole,bupirimate, calcium polysulfide, captafol, captan, carbendazim,carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil,chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate,copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprousoxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil,dazomet, debacarb, diammonium ethylenebis-(dithiocarbamate),dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran,diethofencarb, difenoconazole, difenzoquat ion, diflumetorim,dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton,dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine,dodine free base, edifenphos, enestrobin, epoxiconazole, ethaboxam,ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil,fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate,fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph,fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole,flusilazole, flusulfamide, flutianil, flutolanil, flutriafol,fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium,fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates,GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalilsulfate, imibenconazole, iminoctadine, iminoctadine triacetate,iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone,iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam,isotianil, kasugamycin, kasugamycin hydrochloride hydrate,kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb,mepanipyrim, mepronil, mercuric chloride, mercuric oxide, mercurouschloride, metalaxyl, mefenoxam, meptyl-dinocap, metalaxyl-M, metam,metam-ammonium, metam-potassium, metam-sodium, metconazole,methasulfocarb, methyl iodide, methyl isothiocyanate, metiram,metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam,nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fattyacids), orysastrobin, oxadixyl, oxine-copper, oxpoconazole fumarate,oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen,pentachlorophenol, pentachlorophenyl laurate, penthiopyrad,phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin,polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassiumhydroxyquinoline sulfate, probenazole, prochloraz, procymidone,propamocarb, propamocarb hydrochloride, propiconazole, propineb,proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin,pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox,pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen,quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam,simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodiumpentachlorophenoxide, spiroxamine, sulfur, SYP-Z071, SYP-Z048, tar oils,tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole,thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl,tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole,tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram,zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp.,Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp.,(RS)—N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide,1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate,1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane,2-(2-heptadecyl-2-imidazolin-1-yl)ethanol,2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide,2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride,2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine,4-(2-nitroprop-1-enyl)phenyl thiocyanateme, ampropylfos, anilazine,azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox,bentaluron, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl,bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmiumcalcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone,chloraniformethan, chlorfenazole, chlorquinox, climbazole, cyclafuramid,cypendazole, cyprofuram, decafentin, dichlone, dichlozoline,diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon,dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, ESBP, etaconazole,etem, ethirim, fenaminosulf, fenapanil, fenitropan, 5-fluorocytosine andprofungicides thereof, fluotrimazole, furcarbanil, furconazole,furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin,halacrinate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos,isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam,methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride,myclozolin, N-3,5-dichlorophenyl-succinimide,N-3-nitrophenylitaconimide, natamycin,N-ethylmercurio-4-toluenesulfonanilide, nickelbis(dimethyldithiocarbamate), OCH, phenylmercurydimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, picolinamideUK-2A and derivatives thereof, prothiocarb; prothiocarb hydrochloride,pyracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol;quinacetol sulfate, quinazamid, quinconazole, rabenzazole,salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen,thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos,triarimol, triazbutil, trichlamide, urbacid, and zarilamide, and anycombinations thereof.

Additionally, the compounds of the present invention may be combinedwith other pesticides, including insecticides, nematocides, miticides,arthropodicides, bactericides or combinations thereof that arecompatible with the compounds of the present invention in the mediumselected for application, and not antagonistic to the activity of thepresent compounds to form pesticidal mixtures and synergistic mixturesthereof. The fungicidal compounds of the present disclosure may beapplied in conjunction with one or more other pesticides to control awider variety of undesirable pests. When used in conjunction with otherpesticides, the presently claimed compounds may be formulated with theother pesticide(s), tank mixed with the other pesticide(s) or appliedsequentially with the other pesticide(s). Typical insecticides include,but are not limited to: antibiotic insecticides such as allosamidin andthuringiensin; macrocyclic lactone insecticides such as spinosad andspinetoram; avermectin insecticides such as abamectin, doramectin,emamectin, eprinomectin, ivermectin and selamectin; milbemycininsecticides such as lepimectin, milbemectin, milbemycin oxime andmoxidectin; arsenical insecticides such as calcium arsenate, copperacetoarsenite, copper arsenate, lead arsenate, potassium arsenite andsodium arsenite; botanical insecticides such as anabasine, azadirachtin,d-limonene, nicotine, pyrethrins, cinerins, cinerin I, cinerin II,jasmolin I, jasmolin II, pyrethrin I, pyrethrin II, quassia, rotenone,ryania and sabadilla; carbamate insecticides such as bendiocarb andcarbaryl; benzofuranyl methylcarbamate insecticides such as benfuracarb,carbofuran, carbosulfan, decarbofuran and furathiocarb;dimethylcarbamate insecticides dimitan, dimetilan, hyquincarb andpirimicarb; oxime carbamate insecticides such as alanycarb, aldicarb,aldoxycarb, butocarboxim, butoxycarboxim, methomyl, nitrilacarb, oxamyl,tazimcarb, thiocarboxime, thiodicarb and thiofanox; phenylmethylcarbamate insecticides such as allyxycarb, aminocarb, bufencarb,butacarb, carbanolate, cloethocarb, dicresyl, dioxacarb, EMPC,ethiofencarb, fenethacarb, fenobucarb, isoprocarb, methiocarb,metolcarb, mexacarbate, promacyl, promecarb, propoxur, trimethacarb, XMCand xylylcarb; dessicant insecticides such as boric acid, diatomaceousearth and silica gel; diamide insecticides such as chlorantraniliprole,cyantraniliprole and flubendiamide; dinitrophenol insecticides such asdinex, dinoprop, dinosam and DNOC; fluorine insecticides such as bariumhexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicateand sulfluramid; formamidine insecticides such as amitraz,chlordimeform, formetanate and formparanate; fumigant insecticides suchas acrylonitrile, carbon disulfide, carbon tetrachloride, chloroform,chloropicrin, para-dichlorobenzene, 1,2-dichloropropane, ethyl formate,ethylene dibromide, ethylene dichloride, ethylene oxide, hydrogencyanide, iodomethane, methyl bromide, methylchloroform, methylenechloride, naphthalene, phosphine, sulfuryl fluoride andtetrachloroethane; inorganic insecticides such as borax, calciumpolysulfide, copper oleate, mercurous chloride, potassium thiocyanateand sodium thiocyanate; chitin synthesis inhibitors such asbistrifluoron, buprofezin, chlorfluazuron, cyromazine, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, penfluoron, teflubenzuron and triflumuron; juvenilehormone mimics such as epofenonane, fenoxycarb, hydroprene, kinoprene,methoprene, pyriproxyfen and triprene; juvenile hormones such asjuvenile hormone I, juvenile hormone II and juvenile hormone III;moulting hormone agonists such as chromafenozide, halofenozide,methoxyfenozide and tebufenozide; moulting hormones such as α-ecdysoneand ecdysterone; moulting inhibitors such as diofenolan; precocenes suchas precocene I, precocene II and precocene III; unclassified insectgrowth regulators such as dicyclanil; nereistoxin analogue insecticidessuch as bensultap, cartap, thiocyclam and thiosultap; nicotinoidinsecticides such as flonicamid; nitroguanidine insecticides such asclothianidin, dinotefuran, imidacloprid and thiamethoxam; nitromethyleneinsecticides such as nitenpyram and nithiazine; pyridylmethyl-amineinsecticides such as acetamiprid, imidacloprid, nitenpyram andthiacloprid; organochlorine insecticides such as bromo-DDT, camphechlor,DDT, pp′-DDT, ethyl-DDD, HCH, gamma-HCH, lindane, methoxychlor,pentachlorophenol and TDE; cyclodiene insecticides such as aldrin,bromocyclen, chlorbicyclen, chlordane, chlordecone, dieldrin, dilor,endosulfan, alpha-endosulfan, endrin, HEOD, heptachlor, HHDN, isobenzan,isodrin, kelevan and mirex; organophosphate insecticides such asbromfenvinfos, chlorfenvinphos, crotoxyphos, dichlorvos, dicrotophos,dimethylvinphos, fospirate, heptenophos, methocrotophos, mevinphos,monocrotophos, naled, naftalofos, phosphamidon, propaphos, TEPP andtetrachlorvinphos; organothiophosphate insecticides such asdioxabenzofos, fosmethilan and phenthoate; aliphatic organothiophosphateinsecticides such as acethion, amiton, cadusafos, chlorethoxyfos,chlormephos, demephion, demephion-O, demephion-S, demeton, demeton-Odemeton-S, demeton-methyl, demeton-O-methyl, demeton-S-methyl,demeton-S-methylsulphon, disulfoton, ethion, ethoprophos, IPSP,isothioate, malathion, methacrifos, oxydemeton-methyl, oxydeprofos,oxydisulfoton, phorate, sulfotep, terbufos and thiometon; aliphaticamide organothiophosphate insecticides such as amidithion, cyanthoate,dimethoate, ethoate-methyl, formothion, mecarbam, omethoate, prothoate,sophamide and vamidothion; oxime organothiophosphate insecticides suchas chlorphoxim, phoxim and phoxim-methyl; heterocyclicorganothiophosphate insecticides such as azamethiphos, coumaphos,coumithoate, dioxathion, endothion, menazon, morphothion, phosalone,pyraclofos, pyridaphenthion and quinothion; benzothiopyranorganothiophosphate insecticides such as dithicrofos and thicrofos;benzotriazine organothiophosphate insecticides such as azinphos-ethyland azinphos-methyl; isoindole organothiophosphate insecticides such asdialifos and phosmet; isoxazole organothiophosphate insecticides such asisoxathion and zolaprofos; pyrazolopyrimidine organothiophosphateinsecticides such as chlorprazophos and pyrazophos; pyridineorganothiophosphate insecticides such as chlorpyrifos andchlorpyrifos-methyl; pyrimidine organothiophosphate insecticides such asbutathiofos, diazinon, etrimfos, lirimfos, pirimiphos-ethyl,pirimiphos-methyl, primidophos, pyrimitate and tebupirimfos; quinoxalineorganothiophosphate insecticides such as quinalphos andquinalphos-methyl; thiadiazole organothiophosphate insecticides such asathidathion, lythidathion, methidathion and prothidathion; triazoleorganothiophosphate insecticides such as isazofos and triazophos; phenylorganothiophosphate insecticides such as azothoate, bromophos,bromophos-ethyl, carbophenothion, chlorthiophos, cyanophos, cythioate,dicapthon, dichlofenthion, etaphos, famphur, fenchlorphos, fenitrothionfensulfothion, fenthion, fenthion-ethyl, heterophos, jodfenphos,mesulfenfos, parathion, parathion-methyl, phenkapton, phosnichlor,profenofos, prothiofos, sulprofos, temephos, trichlormetaphos-3 andtrifenofos; phosphonate insecticides such as butonate and trichlorfon;phosphonothioate insecticides such as mecarphon; phenylethylphosphonothioate insecticides such as fonofos and trichloronat;phenyl phenylphosphonothioate insecticides such as cyanofenphos, EPN andleptophos; phosphoramidate insecticides such as crufomate, fenamiphos,fosthietan, mephosfolan, phosfolan and pirimetaphos;phosphoramidothioate insecticides such as acephate, isocarbophos,isofenphos, isofenphos-methyl, methamidophos and propetamphos;phosphorodiamide insecticides such as dimefox, mazidox, mipafox andschradan; oxadiazine insecticides such as indoxacarb; oxadiazolineinsecticides such as metoxadiazone; phthalimide insecticides such asdialifos, phosmet and tetramethrin; pyrazole insecticides such astebufenpyrad, tolefenpyrad; phenylpyrazole insecticides such asacetoprole, ethiprole, fipronil, pyrafluprole, pyriprole andvaniliprole; pyrethroid ester insecticides such as acrinathrin,allethrin, bioallethrin, barthrin, bifenthrin, bioethanomethrin,cyclethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin,deltamethrin, dimefluthrin, dimethrin, empenthrin, fenfluthrin,fenpirithrin, fenpropathrin, fenvalerate, esfenvalerate, flucythrinate,fluvalinate, tau-fluvalinate, furethrin, imiprothrin, meperfluthrin,metofluthrin, permethrin, biopermethrin, transpermethrin, phenothrin,prallethrin, profluthrin, pyresmethrin, resmethrin, bioresmethrin,cismethrin, tefluthrin, terallethrin, tetramethrin, tetramethylfluthrin,tralomethrin and transfluthrin; pyrethroid ether insecticides such asetofenprox, flufenprox, halfenprox, protrifenbute and silafluofen;pyrimidinamine insecticides such as flufenerim and pyrimidifen; pyrroleinsecticides such as chlorfenapyr; tetramic acid insecticides such asspirotetramat; tetronic acid insecticides such as spiromesifen; thioureainsecticides such as diafenthiuron; urea insecticides such as flucofuronand sulcofuron; and unclassified insecticides such as closantel, coppernaphthenate, crotamiton, EXD, fenazaflor, fenoxacrim, hydramethylnon,isoprothiolane, malonoben, metaflumizone, nifluridide, plifenate,pyridaben, pyridalyl, pyrifluquinazon, rafoxanide, sulfoxaflor,triarathene and triazamate, and any combinations thereof.

Additionally, the compounds of the present invention may be combinedwith herbicides that are compatible with the compounds of the presentinvention in the medium selected for application, and not antagonisticto the activity of the present compounds to form pesticidal mixtures andsynergistic mixtures thereof. The fungicidal compounds of the presentdisclosure may be applied in conjunction with one or more herbicides tocontrol a wide variety of undesirable plants. When used in conjunctionwith herbicides, the presently claimed compounds may be formulated withthe herbicide(s), tank mixed with the herbicide(s) or appliedsequentially with the herbicide(s). Typical herbicides include, but arenot limited to: amide herbicides such as allidochlor, beflubutamid,benzadox, benzipram, bromobutide, cafenstrole, CDEA, cyprazole,dimethenamid, dimethenamid-P, diphenamid, epronaz, etnipromid,fentrazamide, flupoxam, fomesafen, halosafen, isocarbamid, isoxaben,napropamide, naptalam, pethoxamid, propyzamide, quinonamid and tebutam;anilide herbicides such as chloranocryl, cisanilide, clomeprop,cypromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican,mefenacet, mefluidide, metamifop, monalide, naproanilide, pentanochlor,picolinafen and propanil; arylalanine herbicides such as benzoylprop,flamprop and flamprop-M; chloroacetanilide herbicides such asacetochlor, alachlor, butachlor, butenachlor, delachlor, diethatyl,dimethachlor, metazachlor, metolachlor, S-metolachlor, pretilachlor,propachlor, propisochlor, prynachlor, terbuchlor, thenylchlor andxylachlor; sulfonanilide herbicides such as benzofluor, perfluidone,pyrimisulfan and profluazol; sulfonamide herbicides such as asulam,carbasulam, fenasulam and oryzalin; thioamide herbicides such aschlorthiamid; antibiotic herbicides such as bilanafos; benzoic acidherbicides such as chloramben, dicamba, 2,3,6-TBA and tricamba;pyrimidinyloxybenzoic acid herbicides such as bispyribac andpyriminobac; pyrimidinylthiobenzoic acid herbicides such as pyrithiobac;phthalic acid herbicides such as chlorthal; picolinic acid herbicidessuch as aminopyralid, clopyralid and picloram; quinolinecarboxylic acidherbicides such as quinclorac and quinmerac; arsenical herbicides suchas cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassiumarsenite and sodium arsenite; benzoylcyclohexanedione herbicides such asmesotrione, sulcotrione, tefuryltrione and tembotrione; benzofuranylalkylsulfonate herbicides such as benfuresate and ethofumesate;benzothiazole herbicides such as benzazolin; carbamate herbicides suchas asulam, carboxazole chlorprocarb, dichlormate, fenasulam, karbutilateand terbucarb; carbanilate herbicides such as barban, BCPC, carbasulam,carbetamide, CEPC, chlorbufam, chlorpropham, CPPC, desmedipham,phenisopham, phenmedipham, phenmedipham-ethyl, propham and swep;cyclohexene oxime herbicides such as alloxydim, butroxydim, clethodim,cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim andtralkoxydim; cyclopropylisoxazole herbicides such as isoxachlortole andisoxaflutole; dicarboximide herbicides such as cinidon-ethyl, flumezin,flumiclorac, flumioxazin and flumipropyn; dinitroaniline herbicides suchas benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin,isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin,prodiamine, profluralin and trifluralin; dinitrophenol herbicides suchas dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen andmedinoterb; diphenyl ether herbicides such as ethoxyfen; nitrophenylether herbicides such as acifluorfen, aclonifen, bifenox,chlomethoxyfen, chlornitrofen, etnipromid, fluorodifen, fluoroglycofen,fluoronitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen,nitrofluorfen and oxyfluorfen; dithiocarbamate herbicides such asdazomet and metam; halogenated aliphatic herbicides such as alorac,chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methylbromide, monochloroacetic acid, SMA and TCA; imidazolinone herbicidessuch as imazamethabenz, imazamox, imazapic, imazapyr, imazaquin andimazethapyr; inorganic herbicides such as ammonium sulfamate, borax,calcium chlorate, copper sulfate, ferrous sulfate, potassium azide,potassium cyanate, sodium azide, sodium chlorate and sulfuric acid;nitrile herbicides such as bromobonil, bromoxynil, chloroxynil,dichlobenil, iodobonil, ioxynil and pyraclonil; organophosphorusherbicides such as amiprofos-methyl, anilofos, bensulide, bilanafos,butamifos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glufosinate-P,glyphosate and piperophos; phenoxy herbicides such as bromofenoxim,clomeprop, 2,4-DEB, 2,4-DEP, difenopenten, disul, erbon, etnipromid,fenteracol and trifopsime; oxadiazoline herbicides such as methazole,oxadiargyl, oxadiazon; oxazole herbicides such as fenoxasulfone;phenoxyacetic herbicides such as 4-CPA, 2,4-D, 3,4-DA, MCPA,MCPA-thioethyl and 2,4,5-T; phenoxybutyric herbicides such as 4-CPB,2,4-DB, 3,4-DB, MCPB and 2,4,5-TB; phenoxypropionic herbicides such ascloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop,mecopropand mecoprop-P; aryloxyphenoxypropionic herbicides such aschlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop,fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop,haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop,quizalofop-P and trifop; phenylenediamine herbicides such as dinitramineand prodiamine; pyrazole herbicides such as pyroxasulfone;benzoylpyrazole herbicides such as benzofenap, pyrasulfotole,pyrazolynate, pyrazoxyfen, and topramezone; phenylpyrazole herbicidessuch as fluazolate, nipyraclofen, pioxaden and pyraflufen; pyridazineherbicides such as credazine, pyridafol and pyridate; pyridazinoneherbicides such as brompyrazon, chloridazon, dimidazon, flufenpyr,metflurazon, norflurazon, oxapyrazon and pydanon; pyridine herbicidessuch as aminopyralid, cliodinate, clopyralid, dithiopyr, fluoroxypyr,haloxydine, picloram, picolinafen, pyriclor, thiazopyr and triclopyr;pyrimidinediamine herbicides such as iprymidam and tioclorim; quaternaryammonium herbicides such as cyperquat, diethamquat, difenzoquat, diquat,morfamquat and paraquat; thiocarbamate herbicides such as butylate,cycloate, di-allate, EPTC, esprocarb, ethiolate, isopolinate,methiobencarb, molinate, orbencarb, pebulate, pro sulfocarb,pyributicarb, sulfallate, thiobencarb, tiocarbazil, tri-allate andvernolate; thiocarbonate herbicides such as dimexano, EXD and proxan;thiourea herbicides such as methiuron; triazine herbicides such asdipropetryn, indaziflam, triaziflam and trihydroxytriazine;chlorotriazine herbicides such as atrazine, chlorazine, cyanazine,cyprazine, eglinazine, ipazine, mesoprazine, procyazine, proglinazine,propazine, sebuthylazine, simazine, terbuthylazine and trietazine;methoxytriazine herbicides such as atraton, methometon, prometon,secbumeton, simeton and terbumeton; methylthiotriazine herbicides suchas ametryn, aziprotryne, cyanatryn, desmetryn, dimethametryn,methoprotryne, prometryn, simetryn and terbutryn; triazinone herbicidessuch as ametridione, amibuzin, hexazinone, isomethiozin, metamitron andmetribuzin; triazole herbicides such as amitrole, cafenstrole, epronazand flupoxam; triazolone herbicides such as amicarbazone, bencarbazone,carfentrazone, flucarbazone, ipfencarbazone, propoxycarbazone,sulfentrazone and thiencarbazone-methyl; triazolopyrimidine herbicidessuch as cloransulam, diclosulam, florasulam, flumetsulam, metosulam,penoxsulam and pyroxsulam; uracil herbicides such as benzfendizone,bromacil, butafenacil, flupropacil, isocil, lenacil, saflufenacil andterbacil; urea herbicides such as benzthiazuron, cumyluron, cycluron,dichloralurea, diflufenzopyr, isonoruron, isouron, methabenzthiazuron,monisouron and noruron; phenylurea herbicides such as anisuron, buturon,chlorbromuron, chloreturon, chlorotoluron, chloroxuron, daimuron,difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron,isoproturon, linuron, methiuron, methyldymron, metobenzuron,metobromuron, metoxuron, monolinuron, monuron, neburon, parafluoron,phenobenzuron, siduron, tetrafluoron and thidiazuron;pyrimidinylsulfonylurea herbicides such as amidosulfuron, azimsulfuron,bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron,flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron,halosulfuron, imazosulfuron, mesosulfuron, metazosulfuron, nicosulfuron,orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron,pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron andtrifloxysulfuron; triazinylsulfonylurea herbicides such aschlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, metsulfuron,prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuronand tritosulfuron; thiadiazolylurea herbicides such as buthiuron,ethidimuron, tebuthiuron, thiazafluoron and thidiazuron; andunclassified herbicides such as acrolein, allyl alcohol,aminocyclopyrachlor, azafenidin, bentazone, benzobicyclon,bicyclopyrone, buthidazole, calcium cyanamide, cambendichlor,chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, cinmethylin,clomazone, CPMF, cresol, cyanamide, ortho-dichlorobenzene, dimepiperate,endothal, fluoromidine, fluridone, fluorochloridone, flurtamone,fluthiacet, indanofan, methyl isothiocyanate, OCH, oxaziclomefone,pentachlorophenol, pentoxazone, phenylmercury acetate, prosulfalin,pyribenzoxim, pyriftalid, quinoclamine, rhodethanil, sulglycapin,thidiazimin, tridiphane, trimeturon, tripropindan and tritac.

Another embodiment of the present disclosure is a method for the controlor prevention of fungal attack. This method comprises applying to thesoil, plant, roots, foliage, seed or locus of the fungus, or to a locusin which the infestation is to be prevented (for example applying tocereal or grape plants), a fungicidally effective amount of one or moreof the compounds of Formula I. The compounds are suitable for treatmentof various plants at fungicidal levels, while exhibiting lowphytotoxicity. The compounds may be useful both in a protectant and/oran eradicant fashion.

The compounds have been found to have significant fungicidal effectparticularly for agricultural use. Many of the compounds areparticularly effective for use with agricultural crops and horticulturalplants. Additional benefits may include, but are not limited to,improving the health of a plant; improving the yield of a plant (e.g.increased biomass and/or increased content of valuable ingredients);improving the vigor of a plant (e.g. improved plant growth and/orgreener leaves); improving the quality of a plant (e.g. improved contentor composition of certain ingredients); and improving the tolerance toabiotic and/or biotic stress of the plant.

It will be understood by those in the art that the efficacy of thecompound for the foregoing fungi establishes the general utility of thecompounds as fungicides.

The compounds have broad ranges of activity against fungal pathogens.Exemplary pathogens may include, but are not limited to, wheat leafblotch (Septoria tritici, also known as Mycosphaerella graminicola),apple scab (Venturia inaequalis), and Cercospora leaf spots of sugarbeets (Cercospora beticola), leaf spots of peanut (Cercosporaarachidicola and Cercosporidium personatum) and other crops, and blacksigatoka of bananas (Mycosphaerella fujiensis). The exact amount of theactive material to be applied is dependent not only on the specificactive material being applied, but also on the particular actiondesired, the fungal species to be controlled, and the stage of growththereof, as well as the part of the plant or other product to becontacted with the compound. Thus, all the compounds, and formulationscontaining the same, may not be equally effective at similarconcentrations or against the same fungal species.

The compounds are effective in use with plants in a disease-inhibitingand phytologically acceptable amount. The term “disease-inhibiting andphytologically acceptable amount” refers to an amount of a compound thatkills or inhibits the plant disease for which control is desired, but isnot significantly toxic to the plant. This amount will generally be fromabout 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm beingpreferred. The exact amount of a compound required varies with thefungal disease to be controlled, the type of formulation employed, themethod of application, the particular plant species, climate conditions,and the like. A suitable application rate is typically in the range fromabout 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per squaremeter, g/m²).

Any range or desired value given herein may be extended or alteredwithout losing the effects sought, as is apparent to the skilled personfor an understanding of the teachings herein.

The compounds of Formula I may be made using well-known chemicalprocedures. Intermediates not specifically mentioned in this disclosureare either commercially available, may be made by routes disclosed inthe chemical literature, or may be readily synthesized from commercialstarting materials utilizing standard procedures.

The following examples are presented to illustrate the various aspectsof the compounds of the present disclosure and should not be construedas limitations to the claims.

Example 1 Preparation of4-(dimethylamino-methyleneamino)-5-fluoro-2-oxo-2H-pyrimidine-1-carboxylicacid 2,2-dimethyl-propyl ester (1)

To an 8 mL screw-cap vial was added dichloromethane (CH₂Cl₂; 3milliliters (mL)),N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (100milligrams (mg), 0.54 millimole (mmol)), triethylamine (Et₃N; 120 mg,1.18 mmol), and 2,2-dimethylpropyl chloroformate (90 mg, 0.60 mmol).After shaking for 1.5 hours (h) at room temperature, the mixture waspartitioned between ethyl acetate (EtOAc) and water (H₂O). The organicphase was dried over magnesium sulfate (MgSO₄), filtered, andevaporated. The crude material was purified by reverse phasechromatography to yield4-(dimethylamino-methyleneamino)-5-fluoro-2-oxo-2H-pyrimidine-1-carboxylicacid 2,2-dimethyl-propyl ester as a white solid (33 mg, 20%): mp162-164° C.; ¹H NMR (300 MHz, CDCl₃) δ 8.77 (s, 1H), 7.93 (d, J=6.6 Hz,1H), 4.08 (s, 2H), 3.27 (s, 3H), 3.20 (s, 3H), 1.05 (s, 9H); ESIMS m/z299 ([M+H]⁺).

Compounds 23-26 were prepared using a similar procedure to Example 1.

Example 2 Preparation of benzyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (2)

To a suspension of 4-amino-5-fluoro-pyrimidin-2-ol* (0.5 g. 3.87 mmol)in acetonitrile (CH₃CN; 10 mL) was addedN,O-bis(trimethylsilyl)acetamide (BSA; 1.42 mL, 5.81 mmol), and themixture was heated to 55° C. for 1.5 h. The resulting solution wascooled to room temperature and to it was added benzyl chloroformate(1.38 mL, 9.67 mmol) causing a slight exotherm. After 10 minutes (min),a white precipitate formed that was allowed to stir at room temperatureovernight. The solid was suction filtered and was washed with diethylether (Et₂O; 2×10 mL), CH₃CN (1×3 mL) and again with Et₂O (2×10 mL) togive benzyl 4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (0.515 g,50%) as a white solid: mp 212-215° C.; ¹H NMR (300 MHz, DMSO-d₆) δ 8.35(s, 1H), 8.07 (s, 1H), 8.04 (d, J=7.25 Hz, 1H), 7.48-7.45 (m, 2H),7.41-7.34 (m, 3H), 5.32 (s, 2H); ESIMS m/z 264 ([M+H]⁺).

*4-Amino-5-fluoro-pyrimidin-2-ol can be purchased commercially.

Example 3 Preparation of ethyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (3)

Using the procedure of Example 2, 4-amino-5-fluoro-pyrimidin-2-ol (0.25g, 1.9 mmol), BSA (1.41 mL, 5.8 mmol) and ethyl chloroformate (0.277 mL,2.9 mmol) were reacted, and the resulting material was purified viareverse phase chromatography (gradient, CH₃CN/H₂O) to give ethyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (0.098 g, 25.6%) as awhite solid: mp 190-193° C.; ¹H NMR (300 MHz, DMSO-d₆) δ 8.29 (s, 1H),8.04-8.01 (m, 2H), 4.27 (q, J=7.25 Hz, 2H), 1.26 (t, J=7.25 Hz, 3H);ESIMS m/z 200 ([M−H]⁻).

Example 4 Preparation of isopropyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (4)

Using the procedure of Example 2, 4-amino-5-fluoro-pyrimidin-2-ol (0.25g, 1.9 mmol), BSA (1.41 mL, 5.8 mmol) and isopropyl chloroformate (1 Msolution in toluene; 2.9 mL, 2.9 mmol) were reacted, and the resultingmaterial was purified via reverse phase chromatography (gradient,CH₃CN/H₂O) to give isopropyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (0.225 g, 55%) as awhite solid: mp 217-219° C.; ¹H NMR (300 MHz, DMSO-d₆) δ 8.28 (s, 1H),8.02-7.99 (m, 2H), 4.97 (septet, J=6.26 Hz, 1H), 1.28 (d, J=6.26 Hz,6H); ESIMS m/z 216 ([M+H]⁺).

Example 5 Preparation of phenyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (5)

To a suspension of 4-amino-5-fluoro-pyrimidin-2-ol (1.0 g, 7.74 mmol) inCH₃CN (20 mL) was added BSA (2.84 mL, 11.61 mmol), and the mixture washeated to 65° C. for 1 h. The resulting solution was cooled to roomtemperature and to it was added phenyl chloroformate (2.4 mL, 19.35mmol) causing a slight exotherm. The mixture was stirred at roomtemperature overnight. The suspension that formed was suction filtered,and the solid was washed with Et₂O (3×10 mL). The solid was suspended inEt₂O (10 mL) for 2 h, was collected via suction filtration and wasair-dried overnight. Phenyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (0.90 g, 47%) wasisolated as a white solid: mp 175-180° C.; ¹H NMR (300 MHz, DMSO-d₆) δ9.25 (br s, 2H), 8.45 (d, J=7.25 Hz, 1H), 7.49-7.43 (m, 2H), 7.35-7.28(m, 3H); ESIMS m/z 250 ([M+H]⁺).

Compounds 6-20 were prepared using a similar procedure to Example 5.

Example 6 Preparation of O-phenyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carbothioate (21)

A 25 mL screw-top vial was charged with 4-amino-5-fluoropyrimidin-2-ol(99.7 mg, 0.772 mmol) and CH₃CN (3 mL). BSA (0.284 mL, 1.16 mmol) wasadded, the vial was capped and the resulting heterogenous mixture wasagitated on a rotary shaker at 65° C. for 80 min. The resulting clearand colorless solution was cooled to room temperature. O-Phenylcarbonochloridothioate (0.118 mL, 0.853 mmol) was added, and thereaction was agitated on a rotary shaker at 65° C. for 15 h. Aftercooling to room temperature, the crude material was diluted with CH₂Cl₂(100 mL) and washed with saturated aqueous sodium chloride (satd aqNaCl) solution (50 mL×2). The organic solution was then dried overNa₂SO₄, filtered, and concentrated in vacuo. The green/brown residue wasthen purified by normal phase chromatography (gradient, 0 to 35% methylalcohol (MeOH)/CH₂Cl₂) to afford O-phenyl4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carbothioate (60.7 mg, 30%) as an85% pure brown solid: mp 113-116° C.; ¹H NMR (400 MHz, DMSO-d₆) δ 8.56(s, 1H), 8.44 (d, J=7.2 Hz, 1H), 8.28 (s, 1H), 7.56-7.48 (m, 2H),7.40-7.33 (m, 1H), 7.27-7.21 (m, 2H); ESIMS m/z 266 ([M+H]⁺).

Example 7 Preparation of pentyl4-(benzyl(methyl)amino)-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (22)

A) To a suspension of 2,4-dichloro-5-fluoropyrimidine (0.30 g, 1.80mmol) in dioxane (3.6 mL) were added N-ethyl-N-isopropylpropan-2-amine(0.23 g, 1.80 mmol) and N-methyl-1-phenylmethanamine (0.24 g, 1.98mmol), and the resulting mixture was stirred at room temperature for 16h. The reaction mixture was diluted with EtOAc (15 mL) and the resultingsolution was washed with H₂O (2×5 mL). The organic phase was dried overNa₂SO₄, filtered, and concentrated in vacuo to a light yellow oil whichwas purified by normal phase chromatography (40 g SiO₂; gradient,EtOAc/hexanes) to give a colorless oil which solidified upon cooling.The solid was dried under high vacuum at 23° C. for 16 h to giveN-benzyl-2-chloro-5-fluoro-N-methylpyrimidin-4-amine (0.34 g, 76%) as awhite solid: mp 47-49° C.; ¹H NMR (300 MHz, CDCl₃) δ 8.18 (d, J=6.4,1H), 7.43-7.23 (m, 5H), 4.82 (s, 2H), 3.17 (d, J=3.3, 3H); EIMS m/z 251(M)⁺.

B) To a suspension ofN-benzyl-2-chloro-5-fluoro-N-methylpyrimidin-4-amine (0.075 g, 0.30mmol) in dioxane/H₂O (1:1, 2 mL total volume) was added potassiumhydroxide (KOH; 0.17 g, 3.0 mmol). The mixture was warmed to 100° C. andstirred for 72 h. The reaction mixture was diluted with H₂O (5 mL), andthe pH was adjusted to 7 with 2 N HCl. The resulting white precipitatewas collected by vacuum filtration, but the majority of the productremained in the aqueous phase. The solid and filtrate were combined andthe solvent was removed by azeotropic distillation with CH₃CN in vacuo.The residue was dissolved/suspended in CH₂Cl₂ (25 mL), adsorbed ontoCelite (3.0 g) and purified by normal phase chromatography (24 g SiO₂;gradient, MeOH/CH₂Cl₂) to give4-(benzylmethylamino)-5-fluoropyrimidin-2-ol (0.016 g, 23%) as a whitesolid: mp 122.8-123.6° C.; ¹H NMR (300 MHz, CDCl₃) δ 12.72 (s, 1H),7.42-7.14 (m, 6H), 4.88 (s, 2H), 3.20 (d, J=3.2, 3H); ESIMS m/z 235(M+2)⁺, 232 (M−H)⁻.

C) To a stirred solution of4-(benzyl(methyl)amino)-5-fluoropyrimidin-2(1H)-one (0.200 g, 0.858mmol) in CH₂Cl₂ (18 mL) were added N-pentyl chloroformate (0.142 g,0.944 mmol) and Et₃N (0.263 mL, 1.88 mmol) at 0° C. The mixture wasallowed to warm to room temperature and stirred an additional 3 h. Thecrude reaction mixture was evaporated to dryness and the residue wastriturated with methyl t-butyl ether (MTBE; 4×5 mL) to removetriethylamine hydrochloride. The combined organic layers were evaporatedin vacuo. The crude product was purified by reverse phasechromatography. Pentyl4-(benzyl(methyl)amino)-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (20.1mg, 6.7%) was isolated as a yellow gum: ¹H NMR (methanol-d₄) δ 8.04 (d,J=6.2 Hz, 1H), 7.38-7.25 (m, 5H), 4.24 (t, J=6.6 Hz, 2H), 3.21 (d, J=3.3Hz, 2H), 1.78-1.65 (m, 3H), 1.37 (dd, J=9.2, 5.5 Hz, 6H), 0.92 (t, J=7.1Hz, 3H); ESIMS m/z 348 ([M+H]⁺).

TABLE I Compounds and Related Characterization Data ¹H NMR (δ, DMSO-d₆)unless mp otherwise Cmpd Structure Appearance (° C.) MS noted 6

off-white solid 172.4-173.6 ESIMS m/z 280 [M + H]⁺ 8.65 (s, 1H), 8.52(s, 1H), 8.31 (d, J = 7.2 Hz, 1H), 7.23 (d, J = 9.0 Hz, 2H), 7.01 (d, J= 9.1 Hz, 2H), 3.78 (s, 3H) 7

white solid 143.2-146.3 ESIMS m/z 284 [M + H]⁺ 8.76 (s, 2H), 8.36 (d, J= 7.2 Hz, 1H), 7.61- 7.50 (m, 2H), 7.42-7.31 (m, 2H) 8

off-white solid 222.5-224.6 ESIMS m/z 284 [M + H]⁺ 8.64 (s, 1H), 8.43(s, 1H), 8.32 (d, J = 7.2 Hz, 1H), 7.64 (d, J = 7.9 Hz, 1H), 7.56-7.31(m, 3H) 9

off-white solid 156.8-158.2 ESIMS m/z 268 [M + H]⁺ 8.71 (s, 1H), 8.61(s, 1H), 8.33 (d, J = 7.3 Hz, 1H), 7.37- 7.29 (m, 4H) 10

pale yellow solid 235-237 ESIMS m/z 264 ([M + H]⁺ 1.0%), 128 ([M −COOC₇H₇]⁻ 99%) 8.65 (s, 1H), 8.52 (s, 1H), 8.30 (d, J = 7.2 Hz, 1H),7.26 (d, J = 8.4 Hz, 2H), 7.22-7.12 (m, 2H), 2.32 (s, 3H) 11

white solid 145.8-146.8 ESIMS m/z 298 [M + H]⁺ 8.52 (s, 1H), 8.32 (s,1H), 8.10 (d, J = 7.2 Hz, 1H), 7.70 (dd, J = 5.4, 3.9 Hz, 1H), 7.52 (dd,J = 5.6, 3.6 Hz, 1H), 7.41 (dd, J = 5.4, 3.9 Hz, 2H), 5.42 (s, 2H) 12

off-white solid 142.8-145.1 ESIMS m/z 308 [M + H]⁺ 8.63 (s, 1H), 8.36(s, 1H), 7.95 (d, J = 6.0 Hz, 1H), 7.43- 7.24 (m, 5H), 4.52 (s, 2H),4.25-4.23 (m, 2H), 3.69-3.62 (m, 2H) 13

off-white solid 240-243 ESIMS m/z 188 ([M + H]⁺, 6.0%), 128 ([M −COOCH₃]⁻ 94%) 8.60 (s, 1H), 8.54 (s, 1H), 8.14 (d, J = 7.2 Hz, 1H), 3.86(s, 3H) 14

off-white solid 145.1-146.3 ESIMS m/z 248 [M − H]⁻ 8.93 (s, 2H), 8.25(d, J = 7.1 Hz, 1H), 4.39 (t, J = 5.9 Hz, 2H), 3.79 (t, J = 6.5 Hz, 2H),2.21- 2.06 (m, 2H) 15

off-white solid 94.2-96.3 ESIMS m/z 231 ([M − H]⁻, 18%), 128 ([M −CO₂CH₂CH₂OCH₃]⁻, 61%) 8.58 (s, 1H), 8.48 (s, 1H), 8.11 (d, J = 7.1 Hz,1H), 4.45- 4.33 (m, 2H), 3.70-3.56 (m, 2H), 3.29 (s, 3H) 16

off-white solid 219.3-221.1 ESIMS m/z 304 ([M + H]⁺, 0.24%), 128 ([M −CO₂CH₂CCl₃]⁻ 99.28%) 8.53 (s, 1H), 8.27 (s, 1H), 8.00 (d, J = 7.1 Hz,1H), 5.09 (s, 2H) 17

off-white solid   258-260.4 ESIMS m/z 214 [M + H]⁺ 9.38 (s, 1H), 8.80(s, 1H), 8.14 (d, J = 6.0 Hz, 1H), 6.06- 5.80 (m, 1H), 5.39-5.32 (m,1H), 5.26-5.20 (m, 1H), 4.62- 4.57 (m, 2H) 18

off-white solid 165.8-168.1 ESIMS m/z 300 [M + H]⁺ 8.62 (s, 1H), 8.43(s, 1H), 8.36 (d, J = 7.2 Hz, 1H), 8.10- 7.93 (m, 3H), 7.87 (d, J = 2.0Hz, 1H), 7.65- 7.53 (m, 2H), 7.49 (dd, J = 8.9, 2.3 Hz, 1H) 19

off-white solid 125.9-128.2 ESIMS m/z 244 [M + H]⁺ 9.51 (s, 1H), 9.22(s, 1H), 8.34 (d, J = 7.1 Hz, 1H), 4.30 (t, J = 6.5 Hz, 2H), 1.72-1.60(m, 2H), 1.44-1.21 (m, 4H), 0.88 (t, J = 7.0 Hz, 3H) 20

white solid 139.8-140.6 ESIMS m/z 242 [M + H]⁺ 8.94 (s, 2H), 8.29-8.10(m, 1H), 5.25-5.20 (m, 1H), 2.04- 1.32 (m, 8H) 23

off-white solid 123.2-124.3 ESIMS m/z 319 ([M + H]⁺) (acetone-d₆) 8.65(s, 1H), 8.22 (d, J = 2.6 Hz, 1H), 7.49 (d, J = 6.5 Hz, 2H), 7.46-7.35(m, 3H), 5.30 (s, 2H), 3.30 (s, 3H), 3.18 (s, 3H) 24

off-white solid   179-181.2 ESIMS m/z 319 ([M + H]⁺) (methanol-d₄) 8.74(s, 1H), 8.24 (d, J = 2.8 Hz, 1H), 7.24 (d, J = 8.3 Hz, 2H), 7.14 (d, J= 8.6 Hz, 2H), 3.25 (s, 3H), 3.20 (s, 3H), 2.35 (s, 3H) 25

gum ESIMS m/z 299 ([M + H]⁺) (CDCl₃) 8.66 (s, 1H), 8.18 (d, J = 2.4 Hz,1H), 4.26 (t, J = 6.7 Hz, 2H), 3.22 (s, 3H), 3.20 (s, 2H), 1.85-1.67 (m,2H), 1.45- 1.28 (m, 4H), 0.91 (dd, J = 9.0, 4.4 Hz, 3H) 26

off-white solid 103.5-104.6 ESIMS m/z 297 ([M + H]⁺) (CDCl₃) 8.70 (s,1H), 8.26 (d, J = 2.2 Hz, 1H), 5.25-5.18 (m, 1H), 3.37 (s, 3H), 3.28 (s,3H), 1.95-1.85 (m, 4H), 1.84- 1.72 (m, 2H), 1.70-1.59 (m, 2H)

Example 8 Evaluation of Fungicidal Activity: Leaf Blotch of Wheat(Mycosphaerella graminicola; anamorph: Septoria tritici; Bayer codeSEPTTR)

Wheat plants (variety Yuma) were grown from seed in a greenhouse in 50%mineral soil/50% soil-less Metro mix until the first leaf was fullyemerged, with 7-10 seedlings per pot. These plants were inoculated withan aqueous spore suspension of Septoria tritici either prior to or afterfungicide treatments. After inoculation the plants were kept in 100%relative humidity (one day in a dark dew chamber followed by two tothree days in a lighted dew chamber) to permit spores to germinate andinfect the leaf. The plants were then transferred to a greenhouse fordisease to develop.

The following table presents the activity of typical compounds of thepresent disclosure when evaluated in these experiments. Theeffectiveness of the test compounds in controlling disease wasdetermined by assessing the severity of disease on treated plants, thenconverting the severity to percent control based on the level of diseaseon untreated, inoculated plants.

In each case of Table I the rating scale is as follows:

% Disease Control Rating  76-100 A 51-75 B 26-50 C  0-25 D Not Tested E

TABLE I One-Day Protectant (1DP) and Three-Day Curative (3DC) Activityof Compounds on SEPTTR at 100 ppm SEPTTR SEPTTR 100 PPM 100 PPM Cmpd 1DP3DC 1 A A 2 A A 3 A A 4 A A 5 A A 6 A A 7 A A 8 A A 9 A A 10 A A 11 A A12 A A 13 A A 14 A A 15 A A 16 A A 17 A A 18 A A 19 A A 20 A A 21 A A 22E E 23 E E 24 E E 25 E E 26 E E

1. A compound of Formula I:

wherein R¹ is: H; C₁-C₆ alkyl optionally substituted with 1-3 R⁴; C₁-C₆alkenyl optionally substituted with 1-3 R⁴; C₃-C₆ alkynyl optionallysubstituted with 1-3 R⁴; phenyl or benzyl wherein each of the phenyl orthe benzyl may be optionally substituted with 1-3 R⁵; or with a 5- or6-membered saturated or unsaturated ring system, or with a 5-6 fusedring system, or with a 6-6 fused ring system each containing 1-3heteroatoms wherein each ring may be optionally substituted with 1-3 R⁵,biphenyl or naphthyl optionally substituted with 1-3 R⁵; —(CHR⁶)_(m)OR⁷;—C(═O)R⁸; —C(═S)R⁸; —S(O)₂R⁸; —C(═O)OR⁸; —C(═S)OR⁸; —(CHR⁶)_(m)N(R⁹)R¹⁰;—C(═O)N(R⁹)R¹⁰; or —C(═S)N(R⁹)R¹⁰; wherein m is an integer 1-3; R² is Hor C₁-C₆ alkyl optionally substituted with R⁴; alternatively R¹ and R²may be taken together to form ═CR¹¹N(R¹²)R¹³; R³ is —C(═O)OR⁸ or—C(═S)OR⁸; R⁴ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₄ haloalkylthio,amino, halothio, C₁-C₃ alkylamino, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylcarbonyl, C₂-C₆ alkylaminocarbonyl, hydroxyl, or C₃-C₆trialkylsilyl, R⁵ is independently halogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, amino, C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₆alkoxycarbonyl, or C₂-C₆ alkylcarbonyl, nitro, hydroxyl, or cyano,halothio; R⁶ is H, C₁-C₆ alkyl, C₁-C₆ alkoxy, phenyl or benzyl whereineach of the phenyl wherein each of the phenyl or the benzyl may beoptionally substituted with 1-3 R⁵; R⁷ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl,C₃-C₆ alkynyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxyalkyl, C₂-C₆ alkylcarbonyl,phenyl or benzyl wherein each of the phenyl or the benzyl may beoptionally substituted with 1-3 R⁵, or with a 5- or 6-membered saturatedor unsaturated ring system, or with a 5-6 fused ring system, or with a6-6 fused ring system each containing 1-3 heteroatoms wherein each ringmay be optionally substituted with 1-3 R⁵, biphenyl or naphthyloptionally substituted with 1-3 R⁵; R⁸ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl,C₃-C₆ alkynyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxyalkyl, —(CH₂)₂OCH₂(C₆H₅),phenyl or benzyl wherein each of the phenyl or the benzyl may beoptionally substituted with 1-3 R⁵; or with a 5- or 6-membered saturatedor unsaturated ring system, or with a 5-6 fused ring system, or with a6-6 fused ring system each containing 1-3 heteroatoms wherein each ringmay be optionally substituted with 1-3 R⁵, biphenyl or naphthyloptionally substituted with 1-3 R⁵; R⁹ is H, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxyalkyl, C₂-C₆ alkylcarbonyl, phenyl or benzylwherein each of the phenyl or the benzyl may be optionally substitutedwith 1-3 R⁵; or with a 5- or 6-membered saturated or unsaturated ringsystem, or with a 5-6 fused ring system, or with a 6-6 fused ring systemeach containing 1-3 heteroatoms wherein each ring may be optionallysubstituted with 1-3 R⁵, biphenyl or naphthyl optionally substitutedwith 1-3 R⁵; R¹⁰ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxyalkyl,C₂-C₆ alkylcarbonyl, benzyl, wherein the benzyl may be optionallysubstituted with 1-3 R⁵; alternatively R⁹ and R¹⁰ may be taken togetherto form a 5- or 6-membered saturated ring containing 1-3 heteroatomswherein each ring may be optionally substituted with 1-3 R⁵; R¹¹ is H orC₁-C₄ alkyl; R¹² is H cyano, hydroxyl, C₁-C₄ alkyl, C₁-C₆ alkoxy, C₂-C₆,alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or the benzylmay be optionally substituted with 1-3 R⁵; or with a 5- or 6-memberedsaturated or unsaturated ring system, or with a 5-6 fused ring system,or with a 6-6 fused ring system each containing 1-3 heteroatoms whereineach ring may be optionally substituted with 1-3 R⁵, biphenyl ornaphthyl optionally substituted with 1-3 R⁵; alternatively R¹¹ and R¹²may be taken together to form a 5- or 6-membered saturated ringcontaining 1-3 heteroatoms wherein each ring may be optionallysubstituted with 1-3 R⁵; R¹³ is H, C₁-C₄ alkyl, C₁-C₆ alkoxy, C₂-C₆,alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or the benzylmay be optionally substituted with 1-3 R⁵, or with a 5- or 6-memberedsaturated or unsaturated ring system, or with a 5-6 fused ring system,or with a 6-6 fused ring system each containing 1-3 heteroatoms whereineach ring may be optionally substituted with 1-3 R⁵, biphenyl ornaphthyl optionally substituted with 1-3 R⁵; and alternatively R¹² andR¹³ may be taken together to form a 5- or 6-membered saturated ringcontaining 1-3 heteroatoms wherein each ring may be optionallysubstituted with 1-3 R⁵.
 2. A composition for the control of a fungalpathogen including the compound of claim 1 and a phytologicallyacceptable carrier material.
 3. The composition of claim 2 wherein thefungal pathogen is Apple Scab (Venturia inaequalis), Leaf Blotch ofWheat (Septoria tritici), Leaf Spot of Sugarbeets (Cercospora beticola),Leaf Spots of Peanut (Cercospora arachidicola and Cercosporidiumpersonatum), and Black Sigatoka of Banana (Mycosphaerella fijiensis). 4.A method for the control and prevention of fungal attack on a plant, themethod including the steps of: applying a fungicidally effective amountof at least one of the compounds of claim 1 to at least one of theplant, an area adjacent to the plant, soil adapted to support growth ofthe plant, a root of the plant, foliage of the plant, and a seed adaptedto produce the plant.